Dimethyl Sulfoxide → 4-(4-Amino-3-(methylthio)phenoxy)-3-nitropyridin-2-amine

HRID 217794

Reaktionsgleichung

Reaktionsgleichung von HRID 217794
[H-].[Na+].CS(C)=O.[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][C:9]=1[S:15][CH3:16].Cl[C:18]1[CH:23]=[CH:22][N:21]=[C:20]([NH2:24])[C:19]=1[N+:25]([O-:27])=[O:26]>O>[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:18]2[CH:23]=[CH:22][N:21]=[C:20]([NH2:24])[C:19]=2[N+:25]([O-:27])=[O:26])=[CH:10][C:9]=1[S:15][CH3:16]

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 40716944-Chloro-3-nitropyridin-2-amineHCID 190483494-Amino-3-(methylsulfanyl)phenol

Produkt 1

HCID 441860954-(4-Amino-3-(methylthio)phenoxy)-3-nitropyridin-2-amineAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Method A2 Sodium hydride (148 mg) was added to dry DMSO (5.5 mL) and the mixture was stirred at RT for 20 minutes under Ar atmosphere. 4-amino-3-(methylthio)phenol (573 mg, 3.7 mmol) was added thereto, and the mixture stirred for 10 more minutes. Next, 4-Chloro-3-nitropyridin-2-amine (3.7 mmol) was added, and the mixture was heated to 100′C and stirred for 3 hours. After cooling down, water was added, and the mixture extracted three times with EtOAc. The combined organic layers were washed first with a saturated aqueous sodium hydrogen carbonate solution then water, dried over MgSO4 and evaporated to afford the title compound (657 mg, 61%) was obtained after purification by chromatography on silica gel (EtOAc-DCM, 1:1) as a red brown solid (Rf 0.56, EtOAc-DCM, 1:1).

Aufarbeitung

  1. stirringthe mixture stirred for 10 more minutes
  2. temperaturethe mixture was heated to 100′C
  3. stirringstirred for 3 hours
  4. temperatureAfter cooling down
  5. extractionthe mixture extracted three times with EtOAc
  6. washThe combined organic layers were washed first with a saturated aqueous sodium hydrogen carbonate solution
  7. dry with materialwater, dried over MgSO4
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-97f4bedf196b4432b5f79c05b4ae6958
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08198279B2

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